Potassium Hydroxide → (1R,3S,5S)-5-(Tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester

HRID 1527431노트

반응식

HRID 1527431 반응식
C([O:3][C:4]([C@@H:6]1[CH2:11][C@:10]2([CH2:12][O:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)[C@@H:8]([CH2:9]2)[N:7]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:5])C.[OH-].[K+]>CO.C1COCC1.O.CCOC(C)=O>[C:23]([O:22][C:20]([N:7]1[C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][C@:10]2([CH2:12][O:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)[C@H:8]1[CH2:9]2)=[O:21])([CH3:26])([CH3:24])[CH3:25]

참가 물질

7

반응물 2

HCID 14797Potassium HydroxideHCID 68284099(1R,3S,5S)-5-(Tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester

생성물 1

HCID 68284002(1R,3S,5S)-5-(Tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of (1R,3S,5S)-5-(tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester (510 mg, 1.38 mmol) in MeOH (2.3 mL), THF (2.3 mL) and water (2.3 mL) was added KOH (155 mg, 2.76 mmol). The reaction was stirred at 60° C. for 45 min. Then allowed to cool to RT and diluted with EtOAc. The layers were separated, the aqueous layer was acidified by addition of HCl (0.1N, until pH 1) and extracted with EtOAc (×2). The organics were dried (Na2SO4), filtered and concentrated. MS (UPLC/MS): 359.4 [M+NH4]+, 340.4 [M−H]−, 386.4 [M+HCOO]−, 681.5 [2M−H]−; tR (HPLC conditions f): 1.84 min.

후처리

  1. temperatureto cool to RT
  2. customThe layers were separated
  3. additionthe aqueous layer was acidified by addition of HCl (0.1N, until pH 1)
  4. extractionextracted with EtOAc (×2)
  5. dry with materialThe organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custom1.84 min.

출처 및 근거

ORD 기록
ord-b689de084e9f43d89c3a1d1a7247940a
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085555B2

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